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$735,000
3 Beds 2 Baths 220222316 MLS
Secluded 2.76 acres with 179 feet of Deschutes River frontage, this 2100+ sq.ft. 3 BR, 2BA home can be yours for $795,000. This home has all the amenities including a high quality 12x16 shed behind the main house. The property sits on a 1.34 acre plot. Included in the sale is an apx. 1.34 acre plot that sits beside it stretches to the river. Vaulted ceilings and lovely wood paneling throughout. Private balcony off master bedroom upstairs. Tractor mower included. Metal roof that should last forever. Watch beautiful sunsets and starry nights as the elk and deer trek across your property. Quiet. Serene. No next door neighbors. sit back, relax, watch the sunsets and fish the slow moving river.

54715 Silver Fox Drive, Bend

Listing courtesy of Bend Properties.

$2,850,000
5 Beds 4 Baths 220222189 MLS
Set above downtown Tumalo on just over 7 acres, this legacy estate in Winston Ranch is the kind of property that rarely comes available. Mornings open to 180-degree Cascade Mountain views, afternoons unfold by the pool, and evenings settle into a private movie theater or the one-of-a-kind office and den wrapped in spectacular woodwork. Freshly updated throughout with new interior and exterior paint, hardwood flooring, new carpet, updated fixtures, and a reworked primary ensuite, the home feels both timeless and ready. The ground-level primary suite frames an incredible mountain view with a large walk-in closet, picture-perfect tub, and dual vanities, while cherry cabinetry and an open-concept kitchen and living space anchor everyday life. A finished shop with bathroom and workspace and a 44' RV bay deliver rare flexibility. HOA-managed underground irrigation, a 1-mile private loop, and an underground dog fence make country living effortless. Call for a private tour.

20180 Winston Loop, Bend

Listing courtesy of Cascade Hasson SIR.

$1,295,000
4 Beds 3 Baths 220221871 MLS
Move-in ready horse property in the heart of Tumalo with stunning Cascade Mountain views and exceptional equestrian amenities. This beautifully updated 4bed/3ba home offers an open-concept layout filled with natural light, featuring quartz countertops, stainless steel appliances, an induction range, woodstove, and a spacious primary suite with vaulted ceilings and a custom tile shower. A second en suite bedroom with private deck access provides ideal flexibility for guests or multigenerational living. The home includes a newer furnace and heat pump, a newer roof, private well with filtration system, and a 3-car tandem garage with workshop space. Set up perfectly for horse enthusiasts with 4.5 acres of irrigation rights, and fully automated underground sprinklers. The fenced and cross-fenced acreage features a 3-stall barn, tack room, hay barn, loafing shed, and additional outbuilding with fenced dog run. Surrounded by mature landscaping and offering outstanding privacy!

19800 Connarn Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,350,000
4 Beds 3 Baths 220220862 MLS
Beautiful country estate on 9.52 acres in desirable Northeast Bend with 2.5 acres of irrigation. Built in 2016, this 2184 sq ft farmhouse offers 4 bedrooms, 2.5 bathrooms, and a welcoming wrap around deck, with the primary suite conveniently located on the main level. The impressive 4,300 sq ft shop is a standout feature, complete with a huge bridge crane for easily moving heavy items. Additional amenities include a charming art studio, a separate office with ADU potential, irrigation pond, RV hookup and various storage sheds. With easy access to Highways 20 & 97, this property offers the perfect blend of country living, convenience, and functionality. A wonderful family property with room for animals, hobbies, equipment storage, and wide-open Central Oregon living.

63639 Gentry Loop, Bend

Listing courtesy of Ninebark Real Estate.

$2,100,000
2 Beds 2 Baths 220221921 MLS
147 ACRES bordering BLM--an extraordinary, one-of-a-kind retreat where adventure & serenity meet, just 15 minutes from Sunriver. Imagine owning your own landmark - THE ROCK - with sweeping 360 degree views then returning to a luxury custom two-story cabin nestled in the woods with a charming loft that enhances its warm, inviting character. Designed in harmony with nature, this exceptional home showcases artisan craftsmanship with hand-carved railings & posts in and out, foraged iron custom lighting, maple flooring, and custom tilework. The dramatic great room features a floor-to-ceiling stacked stone wood-burning fireplace, soaring vaulted pine ceilings, skylights, and abundant windows framing peaceful forest views. The kitchen offers raw-edge granite slab counters and a breakfast bar. Fish the nearby Fall River or venture to ''The Rock'' and beyond - 147 acres! Complete with 2 bedrooms, 2 baths, and a metal roof--your private wilderness sanctuary awaits. Schedule your private showing!

54655 Jack Pine Road, Bend

Listing courtesy of Sunriver Realty.

$1,650,000
4 Beds 3 Baths 220221453 MLS
Sweeping Cascade Mountain views define the setting for this single-level custom home on 4.53 private, fully fenced acres with 3 acres of irrigation rights, minutes from Downtown Bend. Fully remodeled interiors showcase vaulted ceilings, Acacia wood floors, quartz surfaces, a mahogany grand entry, and a dramatic floor-to-ceiling Montana stone fireplace. The expanded primary suite features a light-filled sunroom wrapped in walls of glass, creating an elegant home office, sitting room, or private retreat. Recent enhancements include updated electrical, smart home systems, garage workshop, refined landscaping, metal cross fencing, and new designer primary closet. Designed for luxury acreage living, the property offers a fenced orchard, pond, room for horses, RV parking with hookups, a north electronic gate, four-car garage with climate-controlled gym, and a 1,440 SF shop with 13' doors on its own electric panel. A rare Bend acreage where refined living, privacy, and versatility converge.

61885 Ward Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,250,000
3 Beds 3 Baths 220221576 MLS
Minutes from downtown Bend, but it feels like you've escaped the world. Just over 2 fenced, irrigated acres with professional landscaping -- the kind of place you pull into after a long day and just exhale. The backyard was made for living -- private patio, hot tub, fire pit, water feature, and an outside bar. Inside, everything flows easily with an open floor plan, game room, and a big utility/mud room that actually gets used. The detached garage has a loft and shop area for all your projects. The mother-in-law suite is completely separated from the main living area -- use it as a primary bedroom or run it as an Airbnb for extra income. Three horse stables, a greenhouse, a 29x31 covered carport, and a garden round out the property. There's room here for horses, hobbies, guests, and income -- all on one piece of land. Pristine and one of a kind. Don't miss it.

22539 Martee Lane, Bend

Listing courtesy of Duke Warner Realty ERA Powered.

$2,495,000
4 Beds 6 Baths 220221476 MLS
Sellers will carry up to $500K with a 4% interest rate for the first year! Call for more details! This 18.95 acre Luxury Estate sits in a park like setting with trees, sparkling pond and panoramic mountain views! Offering options for the lifestyle you desire - wellness pavilion, car collection, home business, equestrian, yoga, gym or artist studio! Great Room features dual flanking fireplaces, wood beams, Brazilian cherry floors and bar area for entertaining. Huge Chef's kitchen features slab granite and large picture window and flows into an elegant dining room with climate controlled wine room. Second floor Primary Suite is a private sanctuary w/sitting room, fireplace & covered balcony that showcases the cinematic landscape. Main floor Guest Suite includes a bedroom, bath and Bonus room. Two guest rooms and two office/flex spaces w/private entrances perfect for multigenerational living or work from home. Outbuildings include a 5 bay RV/shop, detached 2 car garage and kennel.

21725 Rickard Road, Bend

Listing courtesy of Cascade Hasson SIR.

$3,750,000
5 Beds 3 Baths 220221468 MLS
A riverfront sanctuary that comes to market once in a generation. Encompassing nearly three acres and 400 feet of low-bank frontage on the Deschutes River, this property represents one of the largest riverfront parcels in all of Bend - set along one of the Northwest's most iconic waterways, with a sweeping stretch of shoreline unlike anything else on the market. The River Home spans nearly 4,000 sq ft with multiple indoor and outdoor living spaces, a private primary wing, and a guest wing - all with unobstructed river views. Here, the Deschutes National Forest is your closest neighbor - and the cherished mountain town of Bend is just minutes away. Step from your back door to cast a line, host a gala, or watch the seasons change from the bank. Family weddings, holiday events, and legendary dinner parties have graced these grounds for years. As the current owners will tell you: no one ever turns down an invitation, and guests are reluctant to leave. It's hard to put a price on magic.

18880 Baker Road, Bend

Listing courtesy of Stellar Realty Northwest.

$1,949,000
3 Beds 5 Baths 220220868 MLS
Some homes are built to live in. This one is built to gather. From the moment you pass through the gate of Sunset View Estates and the Cascade Mountains fill your windshield, you know you've arrived somewhere special & the home delivers at every turn. Outdoor kitchen, covered patios, cascading water feature, fire pit, and exterior fireplace designed for evenings that stretch late into a Central Oregon summer. The bonus room with wet bar, pool table & grand piano included. The kind of space that makes any night feel like an event. Daily life is just as compelling. Radiant heated white oak floors, Brazilian granite, custom builtins, and multiple gas fireplaces throughout. The main level primary ste is a sanctuary private office, balcony, jacuzzi w Cascade Mountain views. 4,596 sq ft, 1.7 private acres, golf course & mountain views. Heated 4-car garage with RV hookup. New roof, fresh paint, move in ready. This is Bend's luxury market at its finest and it's ready now close to city center

20112 Starfire Ridge, Bend

Listing courtesy of Cascade Hasson SIR.

$1,299,000
3 Beds 2 Baths 220220970 MLS
Experience the beauty of Central Oregon living on this picturesque 10-acre property featuring a completely remodeled, turnkey single-level home with sweeping panoramic views of the Cascade Mountains. Designed for comfort and lifestyle, this exceptional acreage offers unforgettable sunsets, lush landscaping, mature fruit trees, established gardens, and irrigation water ideal for hobby farming, animals, or sustainable living. The property is fenced for critters and provides the perfect blend of privacy, functionality, and natural beauty. A spacious barn with flex space above creates more room for guests, a home office, art studio, or creative retreat. Peaceful and private, this one-of-a-kind Bend property captures the essence of country living while still being conveniently located near town amenities, recreation, and outdoor adventure.

21837 Repine Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC.

$1,099,000
3 Beds 3 Baths 220221154 MLS
Nestled on 12.55 acres with a COID canal running through the property, this 2,602 sq ft two-story home offers privacy, space, and a Central Oregon lifestyle. A 30 X 50 shop (1,500 sq ft) includes RV hookups, loft storage, and workspace. Built in 1999, 9ft ceilings and features 3 lower-level bedrooms plus a large upstairs bonus room with full bath ideal as a 4th bedroom or second living space. The primary suite fully remodeled in 2025 with a jetted tub, walk-in shower, and custom closet. Recent updates include new partial interior paint and partial carpet (2026), updated heat pump, and refreshed front & back decks with rear retaining wall (2024). The kitchen offers granite counters and stainless appliances. Features: a pond, underground irrigation (COID 1.83 acres), water pump, irrigated fenced garden area, front, and back with sprinklers, playground set, and a freshly seal-coated driveway and updated insta-hot water (2026). Well and septic in place! Septic & Well reports!

21821 Butler Market, Bend

Listing courtesy of Sunny in Bend 1% Realty.

$1,399,000
4 Beds 3 Baths 220221148 MLS
Tucked away on 3.20 acres in a highly sought-after pocket of SE Bend, this unique property offers space, flexibility, and a prime location just about a mile from Caldera High School. Built in 2006, the 2,258 sq ft two-story home was significantly enhanced by a 2017 addition and renovation, including construction of the attached garage, two upstairs bedrooms, and remodeled kitchen and primary bathroom. The versatile layout now offers 3 bedrooms plus an office/den ideal for guests, remote work, or flex space. The property also features 2 acres of irrigation, RV electrical hookups, back patio pizza oven, and two accessory structures including a large 48x40 shop, and guest house, providing abundant room for storage, hobbies, equipment, or recreational use. Set on a private rural lot just minutes from SE Bend amenities, schools, and outdoor recreation, this property blends lifestyle, usability, and opportunity in one of Bend's most desirable growth areas.

20735 Mini Lane, Bend

Listing courtesy of eXp Realty, LLC.

$1,308,530
3 Beds 5 Baths 220220976 MLS
This Mediterranean inspired estate captures the Bend lifestyle, set at the end of a quiet lane on two private acres just minutes from town. Surrounded by EFU land and a tranquil canal, enjoy exceptional privacy, wildlife, and sweeping views from Cascade sunsets to Ochoco sunrises. A seasonal 20 foot waterfall, lush lawns, and a secluded patio with hot tub create a true high desert retreat. Inside, formal living and dining flow into a well appointed kitchen with dual dishwashers and passthrough windows. Spacious upstairs bedrooms include a primary suite with private balcony, heated floors, and a jetted soaking tub. Flexible living with a guest suite featuring its own entrance, bath and kitchenette, plus a family room with pool table and a loft area with wood stove. Large pull through garage with 14 foot door for RV, boat, and all your Central Oregon gear. Owner carry terms available.

21283 Dove Lane, Bend

Listing courtesy of RE/MAX Key Properties.

$459,000
220220928 MLS
There's a stretch of Central Oregon between Sisters and Bend where the pines fade into juniper under wide open high desert sky. The mountains pop through the trees, and from a second story, the views stretch from Broken Top to Mount Jefferson. These 4.77 acres sit right in the middle of it, ten minutes from Sisters and twenty from Bend. It's a hard location to beat as a home base for everything Central Oregon has to offer. The land is mostly level with a gentle east-to-west slope that makes building straightforward. Septic test pits have been dug, power lines run along the western edge, and with MUA-10 zoning you can skip the conditional use permit process and move straight into building a home. For someone who wants acreage, a view corridor, and room to build something that fits the landscape rather than fights it, this one's worth a closer look.

67372 Harrington Loop Road, Bend

Listing courtesy of Ponderosa Properties.

$729,000
2 Beds 2 Baths 220220908 MLS
Set on 2.4 acres in Tumalo, life here unfolds with the rhythm of the high desert, sun-drenched mornings, wide open skies and evenings spent beneath a blanket of stars. Views stretch toward the Ochoco Mountains and Smith Rock, while the land invites movement, creativity and possibility. Newly constructed by Titan Steel Structures & High Desert Builders, this property offers over 3,000 sqft of usable floor space centered around a 1 bed/1 bath barndominium connected to an expansive shop with a 15-foot garage door and its own full bathroom. Above, a 900 sqft loft provides space for a studio, workspace or retreat. High-performance features including R-51 insulation and energy-efficient heat pumps in the home and shop ensure year-round comfort and efficiency. A new septic system has capacity for an additional dwelling, opening the door to what comes next. Create a private bike park or disc golf course, design your own retreat or build your next home alongside this incredible foundation.

65450 76th Street, Bend

Listing courtesy of Varsity Real Estate.

$1,300,000
4 Beds 5 Baths 220220840 MLS
Set on a canal flowing directly into the Deschutes River, this one-of-a-kind property offers solitude, river access, and breathtaking Mt. Bachelor views across pristine wetlands, visible from nearly every room. Drop in a kayak and you're on the river in minutes. Wildlife abounds, and evenings by the firepit offer stargazing under a dark sky. A cast stone woodburning fireplace anchors the light-filled living room, which pairs hardwood floors with double-height ceilings and access to a heated Trex deck. In the kitchen, heated floors complement a Monogram range and butler's pantry. The primary suite includes deck access, heated bathroom floors, soaking tub, in-suite laundry, walk-in closet, and adjoining home office. Upstairs are 3 bedrooms - 2 en suite - and a generous bonus room with window seats. A daylight basement adds a workshop, wine cellar, garage door for toys, and lower patio access. A 3-car, 1,000+ sf garage offers ample storage. Minutes from Sunriver and La Pine State Park.

54641 Silver Fox Drive, Bend

Listing courtesy of RE/MAX Key Properties.

$1,245,000
4 Beds 4 Baths 220220803 MLS
Tucked among the pines in Pinewood Country Estates just south of Sunriver, this rare 18.67-acre retreat offers the ultimate Central Oregon lifestyle. Spanning two parcels, the 4,038 sq ft main home and 1,800 sq ft detached ADU/shop create a versatile, multigenerational haven. Inside, enjoy open living with 9' ceilings, a chef's kitchen with 48'' range, oversized fridge/freezer, prep station, wine storage, and seamless flow to an outdoor BBQ. The expansive primary suite features dual bathrooms and three walk-in closets, while guest quarters offer privacy on a separate wing. Multiple flex spaces include a bonus room, office, and all-season room. Outdoors, unwind year-round with a swim spa, hot tub, fire pit, and serene forested surroundings. Gated with RV parking, dog run, and minutes to Sunriver and Bend--this is luxury, space, and adventure combined. Don't wait, schedule your tour today!

17045 Shawnee Circle, Bend

Listing courtesy of Cascade Hasson SIR.

$950,000
5 Beds 3 Baths 220220710 MLS
Set on 2.4 private acres in Woodside Ranch, this custom built 5-bedroom estate is offered for the first time by its original owners. Lovingly cared for and rich with potential, the home delivers the kind of space, setting, and solid construction rarely found in today's market. Towering ceilings and abundant natural light create an impressive first impression, while the sunken formal living room with wood-burning fireplace, formal dining area, central kitchen, and intimate family room with wet bar offer timeless gathering spaces. The main level includes a bedroom, full bath, spacious laundry room, and access to the attached 3-car garage. Upstairs, the west-facing primary suite features a jetted tub, full tile shower, and three closets, with generous guest rooms filling the east wing. This home is ready for its next chapter, and is a beautiful blank slate for your personalization and updates.

60309 Tall Pine Avenue, Bend

Listing courtesy of The Agency Bend.

$479,000
220220649 MLS
Rare de-risked 30-acre EFU parcel at 25606 Alfalfa Market Rd. Just 20 mins to downtown Bend. This pristine acreage boasts stunning panoramic views of the Cascade Mountains & Powell Butte. Avoid the usual utility bottlenecks; the groundwork is already done with power, an established well & pump house permitted for domestic use PLUS 1.9 acres of dedicated irrigation, plus an existing shop & greenhouses. Past Deschutes County septic approval history provides a proven development trail to build your custom mountain-view estate, hobby ranch, or equestrian retreat. No HOA or CC&Rs means total freedom. Maximize your financial strategy with Oregon's premier Special Farm Use property tax assessments. Properties of this scale, with views this massive and infrastructure boxes already checked, are a finite asset in Central Oregon. See docs for well log and septic details. Buyer to do due diligence regarding county dwelling criteria.

25606 Alfalfa Market Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,685,000
5 Beds 4 Baths 220220534 MLS
Tumalo Hobby Farm, water rights, and owned solar. Ideally situated in the coveted Golden Triangle. Enjoy unobstructed views of the Cascade Mountains and Smith Rock. The home is designed for both flexibility and true ranch living, this single-level home offers a separate living space for multi-generational living or extended guests, as well as a detached cottage for flexible use. Expansive windows throughout that flood the home with natural light and frame Central Oregon's breathtaking landscape. Warm and inviting, the home features numerous upgrades and living spaces designed for everyday comfort as well as effortless entertaining. Set on just under 21 fully fenced acres, not all acreage needs to be watered and managed. Currently maintaining an easy 6-8 acres of grass. Two barns, horse stalls and a spacious shop provide outstanding functionality for livestock, hobby farming, equipment storage, or workshop space--making this a truly versatile ranch opportunit

20900 SW Young Avenue, Bend

Listing courtesy of Cascade Hasson SIR.

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